5-Day Romantic Getaway in Chicago, USA

Discover the charm of Chicago's city lights and fall in love all over again.

22 April 2023

A romantic trip to Chicago, United States is the perfect opportunity to explore the Windy City together. You can take a stroll along the picturesque Lake Michigan shoreline, indulge in mouth-watering cuisine at award-winning restaurants, and take in the breathtaking views from the Willis Tower. With a wide range of cultural and entertainment options, Chicago provides the ideal backdrop for a memorable romantic getaway.

Save and get deals

Travel plan

Getting latest place information

Day 1

Arriving in the Windy City

Check into the luxurious Waldorf Astoria for a romantic stay
Head to Millennium Park to see the iconic Cloud Gate sculpture
Enjoy a delicious dinner at the Michelin-starred Alinea restaurant
Take a stroll along the Chicago Riverwalk for stunning views of the city skyline
End the night with a cocktail at the swanky rooftop bar, Cindy's

Day 2

Art and Food

Start the day with breakfast at the trendy café, The Allis
Visit the Art Institute of Chicago, one of the best art museums in the world
Grab a bite to eat at the Chicago French Market, a bustling food hall of curated vendors
Take a scenic boat tour on the Chicago River to see the city's architecture
Have a romantic dinner at Boka, a chic restaurant serving contemporary American cuisine

Day 3

Exploring Chicago's Neighborhoods

Have a leisurely brunch at the charming Little Goat Diner in the West Loop
Take a walk through the vibrant Pilsen neighborhood to see colorful murals and graffiti art
Visit Wrigley Field, the iconic home of the Chicago Cubs
Experience the nightlife in Logan Square, home to trendy bars and restaurants
End the night with a nightcap at The Violet Hour, a stylish cocktail bar

Day 4

History and Shopping

Start the day with breakfast at Xoco, a Mexican-inspired café by celebrity chef Rick Bayless
Visit the Field Museum to learn about natural history and ancient civilizations
Take a stroll down the Magnificent Mile for premier shopping and retail therapy
Have a classic Chicago-style hot dog at Portillo's
Catch a theatre show at the legendary Chicago Theatre

Day 5

Farewell, Chicago

Enjoy a farewell breakfast at the quirky Batter & Berries in Lincoln Park
Visit the Navy Pier for carnival rides and stunning views of Lake Michigan
Take a final stroll around the picturesque Lincoln Park Zoo
End the trip with a romantic dinner at the upscale Harry Caray's Italian Steakhouse
Say goodbye to the Windy City with a nightcap at the speakeasy-style The Office.

Length of stay

1 day 2 days 3 days 4 days 5 days

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

How to get there

Plane

The best way to get to Chicago by plane is to fly into O'Hare International Airport or Midway International Airport, both of which are served by major airlines from most major cities in the world. You can check prices and schedules on websites like Expedia or Kayak.

Car

The best way to get to Chicago by car is to take one of the major highways, such as I-90 or I-94, which both run through the city. However, be aware of traffic congestion during peak travel times.

Train

The best way to get to Chicago by train is to take an Amtrak train, which connects the city to other major cities in the United States, such as New York, Washington D.C., and Los Angeles. The main train station in Chicago is Union Station.

Boat

The best way to get to Chicago by boat is to take a ferry from Navy Pier to locations such as Michigan City or St. Joseph. However, this mode of transportation is not as common as the others and may have limited availability depending on the season.

Bus

The best way to get to Chicago by bus is to take a Greyhound bus, which connects the city to most major cities in the United States. The main bus station in Chicago is the Greyhound Station.